An NBA insider believes the Milwaukee Bucks’ controversial deal to acquire nine-time All-Star point guard Damian Lillard numbers among the worst in league history.
The Bucks gave up some major pieces and draft equity to acquire Lillard in a late 2023 offseason trade for Lillard. Despite posting good (if not great) regular season records with Lillard and All-NBA Milwaukee power forward Giannis Antetokounmpo in the fold, the Bucks failed to advance out of the first round in either of their two seasons with Lillard.
A past-his-prime Lillard, now 35, struggled with health issues that caused him to miss multiple games in each playoff series. He tore his Achilles tendon during Milwaukee’s first round series against the Indiana Pacers this past spring.
Bucks general manager Jon Horst stretched and waived the $112.6 million contract the club had owed Lillard over the next two years, which it will now dole out over five seasons. Lillard, who re-signed with the Portland Trail Blazers this summer after being waived, will be paid $22.5 million a year to not play for Milwaukee.
In a fresh piece, Zach Harper of The Athletic wonders if the Bucks’ trade for Lillard ranks among the worst trades in NBA history.
Where do the Bradley Beal and Damian Lillard trades rank among the worst in NBA history? pic.twitter.com/eLKdidQu4T
— The Athletic (@TheAthletic) July 22, 2025
The Bucks dealt away six-time All-Defensive Team guard Jrue Holiday, reserve wing Grayson Allen, a 2029 first round pick, and pick swaps in 2028 and ’30, as part of a three-team deal with the Trail Blazers and Phoenix Suns.
Holiday was promptly traded to the Boston Celtics, and instantly won his second title as a starter there. Portland also added former Phoenix center Deandre Ayton, then-rookie Suns second round pick Toumani Camara, All-Defensive Team Celtics center Robert Williams III, former Boston Sixth Man of the Year Malcolm Brogdon, a 2024 first round pick, and a second 2029 first round pick.
Brogdon and that 2024 selection were traded to the Washington Wizards in exchange for small forward Deni Avdija, who suddenly looks like a borderline All-Star in Portland.
Harper notes that, though the team traded Anfernee Simons to reacquire Holiday this summer and Portland cut Ayton outright after two frustrating season, “Camara has been a revelation for them on defense, making All-Defensive Second Team in his second season after being a second-round pick in 2023.”
Ultimately, because Milwaukee is on the hook for so much money and had such limited success with Lillard, Harper believes the trade is bad — if not “worst trade ever” bad.
“We don’t know what that draft capital owed to Portland will end up being. But we know the Bucks ended up with nothing but dead cap space to show for that deal,” Harper posits. “Milwaukee… probably didn’t make the worst trades ever, but [the Bucks are] in the conversation due to minimal return and the dead cap space that sits for the next half decade.”
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